CH311568A - Process for the production of a new basic substituted fatty acid amide. - Google Patents

Process for the production of a new basic substituted fatty acid amide.

Info

Publication number
CH311568A
CH311568A CH311568DA CH311568A CH 311568 A CH311568 A CH 311568A CH 311568D A CH311568D A CH 311568DA CH 311568 A CH311568 A CH 311568A
Authority
CH
Switzerland
Prior art keywords
ethyl
fatty acid
methyl
production
acid amide
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Cilag
Original Assignee
Cilag Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cilag Ag filed Critical Cilag Ag
Publication of CH311568A publication Critical patent/CH311568A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren     zur    Herstellung eines neuen basisch substituierten     Fettsäureamides.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines neuen       basiseh    substituierten     Fettsäureamides,        wel-          ebes        dadureh    gekennzeichnet ist, dass man auf  eine Verbindung der Formel  
EMI0001.0008     
         eine    Verbindung der Formel  
EMI0001.0010     
    in welchen Formeln X und Y reaktionsfähige,  bei der Reaktion sich abspaltende Reste be  deuten, einwirken lässt.  



  Als Verbindungen der Formel I kommen  für einen Umsatz beispielsweise in Frage:  Das freie Amin (Y = H), aber auch dessen  Salze, wie beispielsweise das Hydrochlorid  oder das Sulfat.  



  Als Verbindungen der Formel     II    kommen       beispielsweise    in Frage:     2-DTethyl-piperidino-          essigsäure    selbst und ihre reaktionsfähigen  funktionellen Derivate wie ihre     Halogenide,     ihre Ester, ihre     Anhydride,    beispielsweise die  reinen und auch die gemischten     Anhydride     mit.     Pllosphorsäure,    Schwefelsäure und     Koh-          leilsallre        usf.     



  Man kann beispielsweise     N-[2-(2'-lIethyl-          phenoxy)-ätllyl-]        ]-N-methylamin    oder auch  ein Salz desselben in Gegenwart eines für  diese Zwecke geeigneten wasserabspaltenden    Mittels wie     Phosphorpentoxyd,        Phosphoroxy-          chlorid        usf.    mit     2-Methyl-piperidino-essig-          säure    behandeln.  



  Weiter kann man auch     N-[2-(2'-Methyl-          phenoxy)-äthyl-1]-N-methylamin    bzw. ein Salz  desselben mit einem     2-Methyl-piperidino-essig-          säurehalogenid    (bzw. einem Salz eines sol  chen) oder einem     Anhydrid    zur Reaktion  bringen.  



  Es ist weiterhin auch möglich,     N-[2-(2'-          Methyl-phenoxy)-äthyl-1]-N-methylamin    mit  einem 2 -     Methyl    -     piperidino    -     essigsäureester,     vorzugsweise einem     Arylester,    bei erhöhter  Temperatur zu     acylieren.     



  Das auf diese Weise erhaltene     N-[2-(2'-          Methyl-phenoxy)-äthyl-1    ]     -1\,T-methyl-2"-ineth@Tl-          piperidino-acetamid    bildet ein farbloses, unter  0,2 mm bei 190-192  siedendes öl.  



  Das neue     Amid    soll als Lokalanästhetikum  und als Zwischenprodukt zur Herstellung wei  terer Derivate Verwendung finden.    <I>Beispiel:</I>  16g     N-[2-(2'-Methyl-phenoxy)-äthyl-1]-N-          methylamin    in Benzol werden mit einer     Mi-          sehung    von 20     g        2-Methyl-piperidino-essig-          säurechlorid-hydrochlorid    und 20 g     Triäthyl-          amin    erwärmt.

   Anschliessend wird das gebil  dete     Triäthylaminhydrochlorid    durch Aus  schütteln mit Wasser entfernt, die Benzol  lösung nach dem Trocknen verdampft     imd     der Rückstand im     Hochvakulun    destilliert.  Man erhält so in     guter    Ausbeute das N-[2-(2'  Methyl-phenoxy) -     äthyl-1    ]     -N-methyl-    2"-me-           thyl-piperidino-acetamid,    welches ein unter  0,2 mm bei 190-192  siedendes farbloses Öl  darstellt.  



  Die Reaktion kann auch ohne     Verdün-          nungs-    und Kondensationsmittel durchgeführt  werden, indem man beispielsweise das     N-[2-          (2'-1@Tethyl-phenoxy)-äthyl-l    ]     -N-methylamin     mit     2-1lethyl-piperidino-essigsäureehlorid-hy-          drochlorid    trocken erhitzt, anschliessend die  Reaktionsmasse mit Wasser verdünnt und in  üblicher Weise aufarbeitet.



  Process for the production of a new basic substituted fatty acid amide. The subject matter of the present patent is a process for the production of a new basic substituted fatty acid amide, which is characterized by the fact that a compound of the formula
EMI0001.0008
         a compound of the formula
EMI0001.0010
    in which formulas X and Y are reactive residues that are split off during the reaction.



  Compounds of the formula I that can be used for conversion are, for example: The free amine (Y = H), but also its salts, such as the hydrochloride or the sulfate, for example.



  Examples of possible compounds of the formula II are: 2-DTethylpiperidinoacetic acid itself and its reactive functional derivatives such as its halides, its esters, its anhydrides, for example the pure and also the mixed anhydrides. Plloosphoric acid, sulfuric acid and carbon sallre etc.



  For example, N- [2- (2'-lethylphenoxy) -ätllyl-]] -N-methylamine or a salt thereof in the presence of a dehydrating agent suitable for this purpose, such as phosphorus pentoxide, phosphorus oxychloride, etc., with 2- Treat methyl piperidino acetic acid.



  It is also possible to use N- [2- (2'-methylphenoxy) ethyl-1] -N-methylamine or a salt thereof with a 2-methyl-piperidino-acetic acid halide (or a salt of one of these) ) or an anhydride to react.



  It is also possible to acylate N- [2- (2'-methyl-phenoxy) -ethyl-1] -N-methylamine with a 2-methyl-piperidino-acetic acid ester, preferably an aryl ester, at elevated temperature.



  The N- [2- (2'-methyl-phenoxy) -ethyl-1] -1 \, T-methyl-2 "-ineth @ Tl-piperidino-acetamide obtained in this way forms a colorless, less than 0.2 mm at 190-192 boiling oil.



  The new amide is to be used as a local anesthetic and as an intermediate for the production of further derivatives. <I> Example: </I> 16 g of N- [2- (2'-methyl-phenoxy) -ethyl-1] -N-methylamine in benzene are mixed with 20 g of 2-methyl-piperidino-acetic acid - heated acid chloride hydrochloride and 20 g triethylamine.

   The formed triethylamine hydrochloride is then removed by shaking with water, the benzene solution is evaporated after drying and the residue is distilled in a high vacuum. The N- [2- (2 'methyl-phenoxy) -ethyl-1] -N-methyl-2 "-methyl-piperidino-acetamide, which has a lower than 0.2 mm at 190- 192 represents boiling colorless oil.



  The reaction can also be carried out without a diluent and condensing agent, for example by mixing N- [2- (2'-1 @ methyl-phenoxy) -ethyl-1] -N-methylamine with 2-1-methyl-piperidino-acetic acid chloride -Hydrochloride heated dry, then the reaction mass diluted with water and worked up in the usual way.

Claims (1)

PATENTANSPRUCII Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, da durch gekennzeichnet, dass man auf eine Ver bindung der Formel EMI0002.0011 eine Verbindung der Formel EMI0002.0012 in welchen Formeln N und V reaktionsfähige, bei der Reaktion sieh abspaltende Reste be deuten, einwirken lässt. Das auf diese Weise erhaltene N-[2-(2'- 1VTethy 1-phenoxy)-äthyl-1 ] -N-methy 1-2"-methyl- piperidino-acetamid ist ein farbloses, unter 0,2 mm bei 190-192 siedendes Öl. PATENT CLAIMS Process for the preparation of a new basic substituted fatty acid amide, characterized in that one is based on a compound of the formula EMI0002.0011 a compound of the formula EMI0002.0012 in which formulas N and V are reactive residues that split off during the reaction. The N- [2- (2'- 1VTethy 1-phenoxy) -ethyl-1] -N-methy 1-2 "-methyl-piperidino-acetamide obtained in this way is a colorless, less than 0.2 mm at 190- 192 boiling oil. Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt Verwendung finden. UNTERANSPRUCH Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man N-[2-(2'-iVlethyl- pheno-xy) -äthyl-1 ] -N-methy lamiii mit einem 2--Iethyl-piperidino-essigsäurehalogenid um setzt. The new amide will be used as a local anesthetic and as an intermediate product. SUBSTANTIAL CLAIM Process according to claim, characterized in that N- [2- (2'-iVlethyl-pheno-xy) -ethyl-1] -N-methy lamiii with a 2-ethyl-piperidino-acetic acid halide is implemented.
CH311568D 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide. CH311568A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311568T 1952-06-08
CH306201T 1955-03-31

Publications (1)

Publication Number Publication Date
CH311568A true CH311568A (en) 1955-11-30

Family

ID=25735095

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311568D CH311568A (en) 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide.

Country Status (1)

Country Link
CH (1) CH311568A (en)

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